Roommates Mom

I'm Jack, 21 a junior in college. I'm good looking and well built. I have always had a way with the ladies. I have the record on the hall for bagging the most babes. My old roommate flunked out last semester and I got a new one, Terry. He is an ok dude, but we don't really click, because he is kind of quiet and not into partying. He spends a lot of time in the library and at his girlfriends so everything is cool. The first weekend his dad and mom dropped off some of his stuff. They are your typical, old, married, power couple. He's some kind of big business exec and his wife owns some kind of interior design company or something. He, the husband is a bit of a dick, but his wife, oh man what a MILF. She's dressed like she just stepped out of a fashion magazine. She is extremely attractive for her age. She was blonde; blue eyed, and had a nice rack. Apparently she works out some because she is in good shape, and an ass that wouldn't quit. I got a boner as soon as I saw her. I tried to play the good boy and helped them unload the kids stuff. They chatted and talked and before they left I heard the MILF say, Terry my work brings me here sometimes and I will check in on you when I am in town. And she did a few times, she usually would take him out to dinner, and one time invited me but I begged off. Well one day Terry comes in and says I'll be gone for a few days, my girlfriend and I are going to the beach. I forgot to mention that apparently his parents didn't approve of his girlfriend so I was sure this was an undercover operation. That's where our story begins.

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Then late the next afternoon I came in from working out at the gym. I get a knock on the door. Well nobody knocks on the door in the dorm, and I thought it was one of the guys messing with me. "So I yell, come on in you pussy, its open."

I hear an "ahem" and turn around. It's Terry's mom, the MILF.

I say, "Oh, sorry Mrs. Johnson, I thought you were? I mean the door is always open. Nobody ever knocks, I thought it was..."

She says, "Calm down Jack, no need to explain. I was in college once. I know how you boys are."

I stammer, "Well I didn't mean any disrespect, I mean I never would..."

"Let's just forget it ever happened, is Terry here?" she says.

"No he's not Mrs. J, sorry." I say as I regain my composure. Damn she handled that real cool.

Oh, well I just popped in at the last minute; I was hoping to surprise him. Do you know where he is?

"He's probably at the library; you know he spends a lot of time there. Let me text him." I text him, -you're mom's here. I'll cover for you but don't answer your phone whatever you do.- "No answer Mrs. J, but they make you put your phones on silent there. I'm sure he'll text back in a minute." and a plan begins to form in my mind. "You're welcome to have a seat until he does and relax, Mrs. J" I say.

"Well I guess that will work, and please call me Elaine. Mrs. J sounds so formal and makes me feel old." and she pulls out the desk chair and sits down, all prim and proper with her legs crossed.

Well ok Elaine, so you are trying to surprise Jack. Is this a special occasion or something?

No, I just had a client that had an unexpected issue I had to come try to resolve at the last minute, but since I was in town I thought I would take Terry out to dinner.

I needed to get as much information as I could, so I said, "So you are going to meet with your client in the morning?"

No, I met with them earlier today. As I said it was so unexpected I came up and was going to go right back, but the meeting took longer than I expected. Since it was so late I thought, I will take Terry out to dinner, get a hotel room and go back in the morning.

"Dang, Terry still hasn't texted back", I say.

"Let me try calling him. He may pick-up when he sees it's me," she says. "No answer."

"I bet his phone is dead. He forgets to charge it all the time," I say. "I know I'll text his girlfriend, sometimes she studies with him."

Elaine asks, "Do they spend a lot of time together?"

Well, yes I guess. If he's not here he's usually at the library or her place.

"So he could be at her place instead of the library?" she asks.

"Well yes but why wouldn't they answer texts there... No, I'm sure they are just busy and haven't looked at their phones. Busy studying I mean." I say coyly.

"Jack you don't have to try and cover for him. I'm a big girl. I know what may be going on. Remember, as I said I was in college once too. I just wish he didn't get so attached. I mean I understand him wanting to have fun, but he should wait till after college to settle down."

Damn, she would rather him sleep around than get serious. And is she insinuating she got busy a lot? I bet guys were knocking on her door all the time. I know I would have been, and I would like to right now. "Well I'm sure they will be done soon, whatever they are doing. You're welcome to stay as long as you like."

She says, "No, I should go. You probably have plans."

"Actually no," I said. "I was just going to grab something to eat." By now it was well into dinner time. I thought this might give her an idea and it did.

"Oh, well could I take you to dinner?" she said.

I decided it would be better if I didn't look too eager, so I say, "no, you don't have to do that. It will be alright. You came to have dinner with Terry, not me."

Well I did, but he's "unavailable". You are not going to make me eat dinner all alone are you?

Since you put it that way it would not be very gentlemanly of me to refuse. I would hate to ruin your evening any more.

Great, you wouldn't go last time I asked, so this is just making up for that and letting me show you how much I appreciate you being a good roommate to my son.

"Just let me change into something nicer and we can go." I immediately take off my shirt and then my pants and start looking in the closet for something to put on.

Elaine says, "Jack, I'm still here in the room."

I turn around so she can see my nice semi hard-on. She does look and her eyes widen and then she looks away embarrassed. And I say calmly and confidently, "sorry Elaine, but we don't have a changing room here. And I'm sure this is not the first time you've seen a man in his underwear. I hope I didn't offend you."

"It's fine, I'm not a prude, but for gosh sake put something on." and laughs.

She is cooler and looser than I thought. My plan may have a chance, I think. I put on the nicest thing I have and we take her car and go to dinner. She takes us to a nice restaurant. It is very upscale and classy. I can tell this is her kind of place. She orders a bottle of wine. She tries calling Terry on her phone, but surprise, no answer.

We drink and eat. I have never been a wine guy so I slowly sip mine, but I keep her glass full. I pretend to top mine off each time, so she won't notice but she drinks most of the bottle. As we sit and eat a leisurely dinner, I ask her where she went to college and she begins to reminisce. She is reliving her carefree younger days. I would prod her with a question now and then and just listen. Women love it when you just listen and let them talk. I could tell she was enjoying it. It was like she was a college co-ed again. Not only was she gorgeous she was delightful. It was perfect. She was far away from her busy life and humdrum marriage.

But the meal ended and the waiter asked if we would like some more wine, or desert. She realized how long we had been there and said, "We should go back to the dorm and see if Terry is back yet."

I said, "wait let me text some of the guys at the dorm and see." After pretending to text, I said, "they say he's not back yet, but I told them to text me as soon as he was. But I have an idea. I know a club he and his girlfriend always go to. I bet they will be there. We could go and it would be an even bigger surprise for him."

"I don't know Jack," she said. "It seems a little weird me going to a college bar. I might feel out of place."

So I say, "You might be a little out of place because you would be the prettiest woman in the place, but it will not be weird, it will be fun."

But, I'm so overdressed.

I had noticed she had a button up sleeveless blouse under her business type jacket. I said, "You could take off your jacket, unbutton the top button of your blouse and you would fit right in." And gave her that come on you know you want to be sexy look.

She laughed and said, "I guess it could be fun."

"We will make it fun. Come on."

She paid the bill and we left. She tried calling Terry another time and got no answer. When we arrived at the club, it was early, not many people in the place. She was quickly able to see that Terry was not there. I said, "It's early; let me get us some drinks. They could be along any minute."

I got to the bar and see my man Jim. I tell him to get me a beer and a glass of wine for my lady. Who is that lady he asks. He doesn't need to know anything other than what I tell him. She's the lady I'm going to be fucking later. He just shakes his head in disbelief.

I return and we sip our drinks talking and waiting on Terry. Then I say, "come on Elaine let's dance."

She says, "Oh, I can't."

"What you can't dance. I pegged you for a good dancer." I say kiddingly.

You know that's not what I mean. Actually I am a good dancer, but I shouldn't

And why shouldn't you? We are at a dance club, you're a good dancer. When was the last time you went dancing? I could see this last question struck a chord. It was if I could read her mind. She was thinking, I can't remember the last time I went dancing.

"Oh what the hell" she says and she drags me onto the dance floor.

Now she wasn't kidding, she is a good dancer. I was dancing with the most beautiful woman in the room and she was dancing playfully and having fun. We both were on cloud nine. Oh I forgot to mention I told my buddy the DJ to play songs from her era. We danced to song after song. And then on cue, he played a slow song. Without missing a beat, I pulled her close. The club had filled up by now and the dance floor was crowded. We had no choice but to dance close.

I felt her tense just a little so I thought I should lighten the mood. I say, "Isn't this fun Elaine, and you thought you weren't going to have a good time."

"Oh, Jack. I haven't had this much fun in a long time. Thank you for making me come and showing me a good time. I hope I haven't ruined your reputation by dancing with an old woman."

"Elaine, you are not an old woman. You are the most beautiful woman in the room and there is no one I would rather be dancing with right now" I said. She leaned in to kiss me, I'm sure of it, but then apparently caught herself.

"I think we should go. It looks as if Terry's not coming." she said.

"Unfortunately, I think you're right Elaine. Let's finish our drinks and go." I had my bartender buddy refill her glass while we were dancing. She didn't notice, and we finished our drinks and left.

With practically the entire bottle of wine at dinner and these two overfilled glasses, Elaine was certainly drunk. She stumbled as we went to the car and I said I should drive. She willingly gave me the keys and I opened the door for her. She stumbled coming to the door and I caught her in my arms. We looked into each other's eyes. I know I could have kissed her right then, but I have found it is more effective to make them long for it. So I helped her into the car.

She said, "You're such a gentleman." and after I got in the car and started to drive off she leaned her head on my shoulder and said, "thank you for a wonderful evening."

"Elaine I can't remember a more enjoyable evening. You are delightful, I wish this night would never end," I said. And put my hand on her knee. She never flinched. Then I said "where is your hotel, I'll drive you there."

She told me the hotel. It was a very nice upscale hotel near the college. As we drove, I started to slide my hand up her leg. She let out a contented sigh, kind of stretched, and parted her legs slightly. I wondered if I even needed the aphrodisiac. I stopped half way up her thigh. I was not going to grope her there in the car. She maybe would reconsider once we left the car; instead I wanted her to long for it. And apparently she did. She shifted in her seat, parted her legs further and started to breathe deeply. I noticed her unbutton another button on her blouse. Apparently the heat was building within her. I could now look over and see a large portion of her breast. They were magnificent. I could feel my dick getting stiff.

We arrived at the hotel. I got her bag out of the back, opened her door and helped her out of the car. She could barely stand on her own. So I put one arm around her and under her armpit to support her as we began to walk. As we walked thru the lobby, she was a little steadier now so I adjusted my grip, slid my hand down and forward cupping the side of her breast. Again she didn't flinch and I think I heard a slight moan. Most of her inhibitions were now gone. My hand covered most of her breast and was clearly visible to the guy working the desk who was intently staring, so I winked at him.

When we got to the room I asked Elaine for the key. She put her arms over my shoulders and draped herself on me. She fumbled in her purse behind my back, and with the joy of a kid at Christmas exclaimed loudly, "oh look, I found it" and giggled. When she leaned back I had to grab her around the waist to keep her from tumbling backward. She looked deeply into my eyes and said, "Oh Jack, thank you for taking such good care of me, you're a sweetie and handsome too." and gave me a quick peck on the lips.

"I can't tell you how glad I am to be able to take care of you." I said as I swiped the room key, opened the door and slid my hand down to her ass, cupped it as I ushered her into the room. She was now accustomed to my hand on practically every part of her body. I further poured it on by saying, "Elaine, I feel like the luckiest man alive to have spent this evening with you. You are a gorgeous, amazing woman"

I threw her bag in the corner and put one arm up on the wall beside her. I leaned in real close, pinning her against the wall and said, "I had such a good time tonight, did you?"

"Oh, Jack it was wonderful. I had such fun. How can I ever..." before she could finish I kissed her, passionately. She resisted only slightly at the very beginning and then kissed me back passionately, and then my tongue found hers.

But apparently she hadn't lost all her inhibition yet, and pulled back and looked at me with an expression I loved. It was a look of wonder, but also indecision and concern. I knew we were close.

She opened her luscious, desirable lips and said, "But Jack I'm your roommates' mom."

"I know," I said and kissed her again. She cut me a little shorter this time.

Then I say, "That's what makes it perfect, Elaine. I could never let anyone find out and continue to stay in the dorm room. You can't let anyone find out. So, we both have equal incentive." And kiss her again. She kisses me back as I can tell she is mulling this over in her mind. I let my hand slide down to her breast. I cup it gently. Then I begin to stroke the side of her breast, and let my thumb graze her nipple. She lets out a soft moan in my mouth.

She still can't let herself go yet, so pushes back gently again and says, ""Jack, I'm old enough to be your mother."

I begin unbuttoning her blouse as she says this. And continue to do so as I look in her beautiful eyes, and softly say, "I know." And kiss her again. I finish unbuttoning her blouse and slide my hand in under her bra. I focus on her nipples this time, rolling it between my first and second finger. She begins to squirm, but pushes me back again.

"But Jack..." she starts to say, but I interrupt her. "Elaine, I don't care how old you are. Our age didn't stop us from having a wonderful evening and it shouldn't stop us now. And you excite me very much. Here, see for yourself." And I take her hand and put it over my pants onto my very hard cock."

I kiss her again, and feel her hand constrict around my cock. I reach down and up under her dress and place my hand on her pussy and feel her soppy wetness. "Apparently our ages don't bother you either." I say as I slowly slide my hand up and down her pussy.

She throws her head back against the wall and says, "Oh Jack." I slide my hand under her panties. I know we are almost home. Then she offers up her last defense. "We shouldn't."

As I begin removing her skirt I whisper in her ear, "I know."